Desymmetrization of 1,3-Diones by Catalytic Enantioselective Condensation with Hydrazine

We present herein an unprecedented desymmetrization of meso 1,3-diones by enantioselective intermolecular condensation. Under the catalysis by a chiral phosphoric acid, a range of readily available 1,3-diones undergo reaction with hydrazines to produce cyclic and acyclic keto-hydrazones bearing an all-carbon quaternary center in high efficiency and enantioselectivity. These compounds are also highly versatile for the preparation of multifunctional building blocks and heterocycles in excellent stereoselectivity.

Automated summary

This method achieves an unprecedented desymmetrization of meso 1,3-diones by enantioselective intermolecular condensation, producing cyclic and acyclic keto-hydrazones with an all-carbon quaternary center in high efficiency and enantioselectivity. The compounds are versatile for preparing multifunctional building blocks and heterocycles with excellent stereoselectivity.